Straight-chain ω-amino-α,β-unsaturated carbonyl compounds: versatile synthons for the synthesis of nitrogen-containing heterocycles via organocatalytic reactions

Abstract

In this review, we elaborate and discuss the recent applications of straight-chain amino-α,β-unsaturated carbonyl compounds as versatile synthons in organocatalytic reactions for the creation of five- and six-membered saturated nitrogen-containing heterocycles.

Base mediated aza-[2 + 1] annulation and regioselective aziridine ring-opening cascade: mild synthesis of functionalized β-amino ketones from cyclic N-sulfonyl aldimines and α-carbonyl sulfonium salts

“… 3 In addition, aza-Michael addition reaction of α , β -unsaturated ketones with amine-based nucleophiles represent another reliable protocol to access β -AKs motifs. 4 In parallel, transition metal-catalyzed reactions, such as coper-catalyzed decarboxylative Mannich reaction, 5 palladium-catalyzed aminocarbonylation, 6 rhodium-catalyzed hydrogenation of β -ketoenamides, 7 and palladium-catalyzed Tsuji–Wacker oxidation of internal allylamines, 8 have been also successfully employed in preparing structurally diverse and synthetically useful β -AKs and their related analogues. Despite great advances have been made for such molecule synthesis, most of those methodologies usually required the use of corresponding pre-functionalized substrates, expensive catalysts, and harsh reaction conditions.…”

Concise synthesis of pyrrolo[3,4-c]quinolines via a P(NMe2)3-catalyzed [4 + 2] annulation followed by a Zn/AcOH-mediated reduction–hydroamination–isomerization

“…However, to the best of our knowledge, the organocatalytic strategy is rarely reported and still highly challenging. 6 Given our recent ongoing interest in the field of organocatalysis, especially phosphine catalysis, for the synthesis of fused cyclic and spirocyclic skeletons, 7 we envision constructing such a valuable skeleton via a phosphine-catalyzed tandem reaction of 2-amino-β-nitrostyrenes and β′-acetoxy allenoates (Scheme 1).…”